Pyridine → (3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1R)-1-(benzylthiocarbonyl)ethyl]-2-azetidinone

HRID 1902144Notes

Reaction equation

HRID 1902144 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@H:15]([C:17](O)=O)[CH3:16])[NH:13][C:12]1=[O:20])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([SH:28])C1C=CC=CC=1.[Cl-].ClC1N(C)[CH2:34][CH2:33][NH+]1C.N1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)Cl>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C@H:15]([C:17]([CH2:39][C:40]2[CH:34]=[CH:33][CH:43]=[CH:42][CH:41]=2)=[S:28])[CH3:16])[NH:13][C:12]1=[O:20])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7509Benzyl mercaptanHCID 9882831(R)-2-[(3S,4S)-3-[(R)-1-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl]propionic acidHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chloride

Product 1

HCID 57101236(3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1R)-1-(benzylthiocarbonyl)ethyl]-2-azetidinoneYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3S ,4S)-3-[(1R)-1-t-Butyldimethylsilyloxyethyl]-4-[(1R)-1-carboxyethyl]-2-azetidinone (995 mg, 3.3 mmol), benzylmercaptan (409 mg, 3.5 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (592 mg, 3.5 mmol) are dissolved in methylene chloride (3 ml), and thereto is added dropwise pyridine (550 mg, 7.0 mmol) under ice-cooling. The mixture is stirred at room temperature for 10 hours. The reaction solution is treated in the same manner as in Reference Example 3 to give (3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1R)-1-(benzylthiocarbonyl)ethyl]-2-azetidinone (868 mg).

Workup

  1. temperaturecooling
  2. additionThe reaction solution is treated in the same manner as in Reference Example 3

Sources & evidence

ORD record
ord-a131b896cdf74374bbfebc47c9b0286f
Source dataset
uspto-grants-1996_11
Patent number
US05578722

Reaction notes

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